HCID 178508457, compound → HCID 178511226, compound

HRID 550186Notes

Reaction equation

HRID 550186 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:20]3[CH2:25][CH2:24][C@H:23]([CH2:26][NH:27]C(=O)OCC4C=CC=CC=4)[CH2:22][CH2:21]3)=[N:9][C:10]=2[C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:5]=[CH:6][N:7]=1>Cl.O>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:20]3[CH2:21][CH2:22][C@H:23]([CH2:26][NH2:27])[CH2:24][CH2:25]3)=[N:9][C:10]=2[C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 178508457HCID 178508457, compound

Product 1

HCID 178511226HCID 178511226, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of benzyl {[trans-4-(8-amino-1-(1H-indol-2-yl)imidazo[1,5-a]pyrazin-3-yl)cyclohexyl]methyl}carbamate (0.163 g, 0.330 mmol) in conc. HCl (5 ml) was stirred at rt overnight. The reaction mixture was diluted with H2O (20 mL), washed with Et2O (30 mL), then basified with 1N NaOH (aq) and extracted with DCM (3×20 mL). The combined extracts were washed with water then dried over Na2SO4 and concentrated in vacuo To afford 0.085 g of desired compound. MS (ES+): m/z 361.30 [MH+].

Workup

  1. washwashed with Et2O (30 mL)
  2. extractionextracted with DCM (3×20 mL)
  3. washThe combined extracts were washed with water
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8459cdaf268412787ac64e64acf7872
Source dataset
uspto-grants-2011_05
Patent number
US07943767B2

Reaction notes

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